4-Nitrophenol → 4-Nitrophenyl 5-(1-hydroxysilinan-1-yl)pentanoate

HRID 530152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530152
[OH:1][Si:2]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[N+:30]([C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1)([O-:32])=[O:31]>C(OCC)(=O)C>[OH:1][Si:2]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][C:36]2[CH:37]=[CH:38][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=2)=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 904175005-(1-Hydroxysilinan-1-yl)pentanoic acid

Produkt 1

HCID 904181924-Nitrophenyl 5-(1-hydroxysilinan-1-yl)pentanoateAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 5-(1-hydroxysilinan-1-yl)pentanoic acid (130 mg, 0.601 mmol) in ethyl acetate (5 mL), N,N′-dicyclohexylcarbodiimide (186 mg, 0.901 mmol) was added. The reaction was stirred under nitrogen at ambient temperature for 30 minutes. After this time, 4-nitrophenol (100 mg, 0.719 mmol) was added, and the reaction was stirred for 16 hours at ambient temperature. After this time, the reaction was filtered to remove any solids, the filter cake was washed with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography eluting with hexanes to 1:3 ethyl acetate/hexanes to afford 4-nitrophenyl 5-(1-hydroxysilinan-1-yl)pentanoate (106 mg, 52%) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 8.26 (dt, J=9.0, 2.5 Hz, 2H), 7.27 (dt, J=9.0, 2.5 Hz, 2H), 2.61 (t, J=7.5 Hz, 2H), 1.84-1.78 (m, 2H), 1.76-1.67 (m, 4H), 1.56-1.44 (m, 4H), 1.40-1.33 (m, 1H), 0.75-0.63 (m, 6H).

Aufarbeitung

  1. stirringthe reaction was stirred for 16 hours at ambient temperature
  2. filtrationAfter this time, the reaction was filtered
  3. customto remove any solids
  4. washthe filter cake was washed with ethyl acetate
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography
  8. washeluting with hexanes to 1:3 ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b82b652907004f7ab9716277ee08c3f5
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09352049B2

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